More Adventurous
by PlrtzGlrb
Summary: Lit. "I read with every broken heart, we should become more adventurous." Series of ficlets exploring Rory's character and the inevitability of Jess.
1. It's A Hit

**Disclaimer**: I do not have any legal claim over the characters of _Gilmore Girls_ or the lyrics from Rilo Kiley's _More Adventurous._

**A/N**: This album has always, always reminded me of Rory for some reason, and I finally decided to do something about it. This will be a series of ficlets structured non-chronologically around Rory's character. All the stories will exist within the same universe. Rory/Jess will be there, too, and with a strong supporting focus on Paris, Luke/Lorelai.

* * *

**It's A Hit**

* * *

Any chimp can play human for a day  
And use his opposable thumbs to iron his uniform;  
And run for office on election day;  
And fancy himself a real decision maker,  
Then deploy more troops than salt in a shaker.

It's a holiday for a hanging, yeah.

* * *

A bunch of pussies.

That's what they were. No guts, no brains, _clearly_ no familiarity with Monty Python's _Meaning of Life_. (Comparing Bush's economy to Mr. Creosote? Right over their heads.)

They told her not to read the comments. The number one rule, they said, of online journalism. "Don't read the comments."

Pussies.

Rory had been scrolling through pages of comments all night long, clicking drop-downs, digging through forums, tracking down every last word printed about her most recent piece. Her colleagues thought she was playing with fire, that she'd get worn down by the crush of unrelenting idiocy, but for Rory, this was catharsis at its finest. A million Mitchum Huntzbergers couldn't hold her down. It was flattering, knowing that so many people were reading her stuff, responding to it, even if the feedback was written largely in moron. She was tickled. She was alive with the glory of intellectual superiority. A girl has got to get her kicks somehow.

She poured herself another glass of Franzia. It was 2am.

She had a deadline in two days, she knew, and probably shouldn't be up (and drinking) this late on a Wednesday, but she was confident in the piece so far. "The Truth About Truthers." (Working title.) She was killing the Obama beat and she knew it. For once in her life, she was in control. No Friday night dinners and dates with Dean commanding her weekends, no curfew, no school, no Life and Death Brigade, no drama. Every day she woke up with one goal in mind - to write compelling pieces with integrity and accuracy - and every day she went to bed knowing she had done so.

It was a fulfilling life. And no, she wasn't seeing anyone.

Those idiots in the comments, though. They provided her a healthy dose of adversity. Rory would write a piece on the Iowa straw poll, the commenters would call Obama a socialist and question Rory's intelligence. Rory would write a piece on the recession, and the commenters would call Obama a socialist and question Rory's intelligence. She had not yet stooped to creating a fake Disqus account in order to lambast them with her brilliance, but the thought had crossed her mind.

She woke up at 8 the next day, hangover free, though groggier than ideal. She pulled on the first shirt she could find ("Buck Fush"), brushed her teeth in a flash, and headed out the door. She was living on a budget and usually gave herself enough time to make coffee in her apartment, but this morning she'd have to grab a cup on the way to work. The cafe on the corner was no Luke's, but it was decent enough.

She liked the North Side of Chicago, she thought, and her cheap but cozy studio. It was temporary, but it felt enough like home. She liked everything about it. She liked the dive bar around the corner where her mom and she had ordered shots of Kahlua just after the move. She liked the commute to work - a walk past old churches, flower shops, that decent cafe, a train to the loop, an elevator to the 23rd floor, a stop in the breakroom for her second cup of the day.

She liked this newfound confidence, too, this sense of power - like she was on the road to something great. To Christiane Amanpour and beyond.

She liked being single.

How strange that this girl who had been given the nickname "Mary" on the first day of Chilton had straddled practically back-to-back relationships from ages 16 to 22. She lost her virginity in the ugliest way, in her childhood bedroom, to a married ex she'd forgotten how to love years before. She stayed with Logan Huntzberger long after his father had dared to crush her spirit, after the Yacht, the DAR. And what a shame, she thought. She did love Logan, and she doesn't regret her time with him for all that she learned about herself. But her mother had instilled in her a sense of independence so strong that it was like dying to feel herself losing it. She mourned the loss of that girl, the one who ate ice cream cones with a dark haired boy so many moons ago and dreamt of reporting from the trenches.

But she was free, now. She was Rory Gilmore. Completely.

* * *

**A/N**: Comments are mucho appreciated.


	2. Does He Love You?

**Does He Love You?**

* * *

Get a real job, keep the wind at your back and the sun on your face.  
All the immediate unknowns are better than knowing this tired and lonely fate.  
Does he love you? Does he love you?  
Will he hold your tiny face in his hands?

Let's not forget ourselves, good friend.  
I am flawed if I'm not free.

* * *

"I think I may have loved you."

God, was she inviting trouble.

She cut her hair, not so long after. She hated looking in the mirror and seeing _that_ girl staring back at her, all doe-eyed and heartbroken. So, she chopped it off.

She kept busy, as was her custom. She hardly ever thought about him - not directly - but when she did it was agony all over.

"I think I may have loved you."

Bullshit, Rory Gilmore. You know yourself better than that.

Thank god for Paris, Rory thought. Paris was her rudder in this sea of unimaginable heartache. An annoying, judgmental, hyper-tense rudder with terrible taste in men, but still. She had Paris, and the paper, and her classes. Her reading tree. The library (oh, the library). Trips home on the weekends, coffee at Luke's - those were harder for her, but she braved it with her new haircut and her superhuman compartmentalization. It was as if she had willed herself to the next chapter in life.

But now he's here. It takes her a moment to process, because this is _Jess_, in the flesh, and she is _terrified_.

Come with him? Come with _him_? And go _where__?_

"Are you crazy?" The words are out there and she's still reeling. His hair is longer. No gel. He seems unwell. She feels for him but shoves that beat to the side to focus on the more pressing matters at hand.

"Probably. Do it. Come with me. Don't think about it."

He smells good.

"I can't do that."

She moves inside, after forgetting momentarily that her things are in boxes. This is not her place anymore. If she wanted to go, she could go.

"You think you can't do it, but you can. You can do whatever you want."

She remembers telling him about as much when he had told her he had no hopes for college. It was crazy to Rory that Jess would ever need a tutor, but it was even crazier when she realized just how dismissive he was about his own potential. Here was a guy who could recite sonnets from memory, devour a novel in a day, clean her mom's rain gutters, and survive on the streets of New York, and he had no concept of his own self worth. It didn't just upset her, it infuriated her.

_He could do whatever he wanted_. Unfortunately, what he wanted right now was to take a mystery road trip with his ex-girlfriend.

"It's not what I want."

"It is. I know you."

Maybe he does. She wants to believe he doesn't, because it will make the next phase of mourning a little bit more bearable. If there is one thing Rory can do, it is lie to herself.

He presses - she rejects him. He leaves her an ultimatum, for good measure.

"Don't say 'no' just to make me stop talking or make me go away. Only say 'no' if you really don't want to be with me."

She knows that if she stops to think about this, let's him in, she'll cave. She would never drop everything and run away with him, but she'd talk him down, invite him to stay the night. Find out what he's been reading, how he's been doing, maybe get him to open up about California, his dad. He would apologize for leaving without saying goodbye. She would understand - not right away, but with time, because Jess and Rory are two sides of the same coin. It's fight or flight with them. She ran away the first time they kissed, just like he ran away the moment he saw an out.

But she needs to hate him right now. He needs to know how this feels. If she doesn't let him go...If she forgives him, will she ever forgive herself?

So he loves her. And she thinks she may have loved him.

But "no" is the easiest word she's said all night.


	3. Portions for Foxes

**Portions for Foxes**

* * *

I know I'm alone if I'm with or without you,  
but just being around you offers me another form of relief.  
When the loneliness leads to bad dreams,  
and the bad dreams lead me to calling you,  
and I call you and say, "C'mere!"

* * *

Her life had once been filled with thoughts of travel and books and Harvard and Lane and not much else.

Kids grow, they change. All Lorelai ever really wanted was for her daughter to be happy, so she swallows the lump of absolute horror in her throat when Rory - her Rory - tells her that she's "keeping things casual" with a boy.

Sure, Lorelai has known her fair share of "casual." She was the Queen of Casual. Casual had been the only option available to a single mother with a strict no-boys-in-the-house policy.

But Rory? Not casual. The opposite of casual, in fact. The most serious girl on the planet.

"We see each other. We see other people, and that's him over there, seeing other people. So it's fine."

"Oh," is all Lorelai can muster. The artist formerly known as the most serious girl on the planet, then.

"We both agreed," Rory insists.

"Okay, you both agreed, then okay. But, aren't you guys sleeping together?" The sudden urge to go full-on Emily Gilmore comes and passes, like a slow wave of nausea.

"Mom. It's college."

Of course, there was nothing about casual sex in the pamphlets they'd picked up on their visit to Yale. There had been nothing about casual sex on Rory's Harvard Dream Board, or on the pro-con lists they'd made when she was deciding among the Ivies, or anywhere else, come to think of it. She tries to rack her brain for indications that this Casual Sex Haver was lurking anywhere under the surface during Rory's previous relationships.

She recalls with some anxiety the first time Rory had ever expressed the desire to Have Sex with a Guy - over Al's take-out, with Jess. But Rory was Serious with Jess. She'd been falling for this guy for a year, broke Dean's heart in the process, and sex seemed like the next logical step for her very serious kid. She wasn't a robot, after all. She was her mother's daughter.

With Dean, things were...well, _serious_ly fucked up. She wonders if that was the turning point. If Rory hated what she had done with him so much that she would be willing to abandon her quasi-Amish ways for casual sex with someone Emily would approve of.

She wants to be this fabulously accepting mom, all calm and collected about it. Even if it breaks her heart.

"Oh, right. College."

"We're both busy. We have class, we have friends. You know, it's good to just keep things cas, have fun. That's it."

_Cas_? Under normal circumstances, she would have mocked her daughter mercilessly for her use of abbrevs, but the joke loses itself on the tip of her tongue. Too crass, even for the queen of comebacks.

"Fun. Sure, I get it. Friends with benefits. No problem. I watch Oprah." Oof. "Are you _sure_ you're cool with this?"

"I'm completely cool with this."

* * *

She is not.

But Rory talks a big game about comfort zones and living outside of them. It all comes back to Christane Amanpour, and she wonders briefly how Christiane would feel about Rory pushing herself to have this authentic college experience. To live life in as many different ways as possible, to test out new perspectives. Rory knows that there are really people in this world in open relationships who are fine with it, and she is determined to be that way, too.

She pushes any feelings of self-doubt or jealousy into a corner way in the back of her mind and tries, really tries to embrace this.

She and Robert are having a so-so date. Her eyes wander every now and then to Logan and his date, getting cozy on a couch, but she doesn't fret over it. This is a party. A college party, full of rich, cultured, exciting young people, and Rory is not going to be the one to bring the room down just because she has a crush on some guy. No, sir.

Logan just can't let it go, though.

"I don't like this," he says.

"Like what?"

"You're here with Robert."

"You're here with Whitney."

"I know!"

"So what's the problem?"

"The problem is, you're here with Robert and it's bothering me. And I don't like that it's bothering me."

Stop, stop. Rory needs him to stop. Because Rory is bothered, too, and she _can't_ be. She's already broken, like, a dozen of the rules in her own Personal Code of Ethics handbook, and she's able to justify it only by invoking the great promise of worldliness. But now Logan is going to ruin that? No.

"Sorry. Do you want us to leave?" Get out with Robert, great plan, Rory.

"No, I want _us_ to leave. You and me."

"I can't do that."

"Oh, you want to spend the rest of the night with Robert instead of me?"

As if. Logan is...well, he's the only person Rory has ever enjoyed sleeping with, for one. (Sample size: two.) Sex with Logan is amazing. _Being _with Logan is amazing. She wants this, this secluded banter. She wants the look on his face when he surprises her, and the rush of excitement she gets when he does, and if she continues down this path she will be doomed.

"I came here with Robert."

"So, dump Robert. I hate Robert."

"He's your friend!"

"So what? I still hate him."

"Logan, you're the one who said-"

"I know what I said."

She swears, if the next words out of his mouth are, "I take it back," she'll personally volunteer for the castration parade. Don't take it back. Don't let him.

"I have to go. I have a date. Enjoy the rest of the party."

And just like that, she's gone. She silently wonders if it will always be like this - her, running away the moment she feels a boy about to get serious. She did it to Dean. She did it to Jess. Does this mean...?

No. Logan is and only ever will be casual for her. An experiment. A form of relief.

He has to be.


End file.
